Methyl chloroformate → HCID 10354936, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (±)-2-(4-nitrophenyl)glycine (20) (Heyns et al., Justus Lieberg's Annalen der Chimie 611:55-56 (1958)) (3.2400 g, 16.5 mmol) and NaOH (0.6611 g, 16.5 mmol) in water (150 mL) were added methyl chloroformate (1.404 mL, 18.2 mmol), 2N NaOH (9.1 mL), and water (6 mL) at 0° C. After adjusting pH to 9 with 2N NaOH (1 mL) and stirring at 25° C. for 17 h, the mixture was basified to pH 10 with 2N NaOH and washed with diethyl ether before it was acidified with 5N HCl in the presence of EtOAc. The organic fractions (1 L) were dried (MgSO4) and evaporated to yield 19 (3.62 g, 86%): mp 152° C.; 1H NMR (DMSO-d6) δ 3.53 (s, 3H, OCH3), 5.35 (d, J=8.7 Hz, 1H, CH), 7.66 (d, J=8.4 Hz, 2H, aromatic), 8.20 (d, J=8.4 Hz, 3H, aromatic and NH). MS (FAB) m/z 255.0.

Provenance & Evidence